The present invention is concerned with novel .alpha.-fluoromethyl tyrosines and esters thereof.
An unsubstituted .alpha.-fluoromethyl-.alpha.-amino alkanoic acid, namely 2-fluoromethylalanine, having the formula: ##STR1## is known [Kollonitsch et al., J. Org. Chem. 40. 3808-9 (1975)]. No specific pharmacological activity for this compound is suggested. This compound (A) is prepared by fluorodehydroxylation of the corresponding 2-hydroxymethylalanine.
.alpha.-Methyl-m-tyrosine and .alpha.-methyl-p-tyrosine are known (U.S. Pat. No. 2,868,818). Their use in pharmaceutical compositions is described in U.S. Pat. No. 3,322,630, U.S. Pat. No. 3,839,585 and Canadian Pat. No. 737,907. L-.alpha.-methyl-p-tyrosine is also used to treat hypertension in pheochromocytoma.
.alpha.-Trifluoromethyl tyrosines are described in U.S. Pat. No. 3,046,300. These compounds deplete norepinephrine in the heart.
.alpha.-Difluoromethyl tyrosines and esters having pharmaceutical activity have been discovered.